Pyrocatechol (BioDeep_00000014388)
Main id: BioDeep_00000002951
human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019
代谢物信息卡片
化学式: C6H6O2 (110.0368)
中文名称: 邻苯二酚, 儿茶酚
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: c1ccc(c(c1)O)O
InChI: InChI=1S/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H
描述信息
Pyrocatechol, often known as catechol or benzene-1,2-diol, is a benzenediol, with formula C6H4(OH)2. It was first prepared in 1839 by H. Reinsch by distilling catechin (the juice of Mimosa catechu). This colourless compound occurs naturally, but about 20000 tons are manufactured each year, mainly as precursors to pesticides, flavors, and fragrances. Its sulfonic acid is often present in the urine of many mammals. Small amounts of catechol occur naturally in fruits and vegetables, along with the enzyme polyphenol oxidase. Upon mixing the enzyme with the substrate and exposure to oxygen (as when a potato or apple is cut), the colorless catechol oxidizes to reddish-brown benzoquinone derivatives. The enzyme is inactivated by adding an acid, such as lemon juice, or by refrigeration. Excluding oxygen also prevents the browning reaction. Catechol melts at 28 °C and boils at 250 °C. It is employed in medicine as an expectorant. The dimethyl ether or veratrol is also used in medicine. Many other pyrocatechin derivatives have been suggested for therapeutic application. Pyrocatechol has also been found to be a microbial metabolite in Escherichia, Mycobacterium and Pseudomonas (PMID:19300498; PMID:25281236).
Constituent of variety foodstuffs especies coffee, cocoa, bread crust, roasted malt and beer; Isolated from various plant sources and by hydrolysis of tannins (CCD). 1,2-Benzenediol is found in many foods, some of which are chervil, black raspberry, swede, and wasabi.
CONFIDENCE standard compound; INTERNAL_ID 120
同义名列表
34 个代谢物同义名
Pyrocatechol suppliers in China; Catechol, 14C-labeled CPD; Catechol dipotassium salt; 1,2-Dihydroxybenzene; Catechol sodium salt; 1,3-Dihydroxybenzene; alpha-Hydroxyphenol; Durafur developer C; Phthalhydroquinone; 1,2-Hydroxybenzene; O-Dihydroxybenzene; Phthalic alcohol; Benzene-1,2-diol; a-Hydroxyphenol; 1,2-Benzenediol; O-Phenylenediol; Α-hydroxyphenol; 2-Hydroxyphenol; O-Hydroxyphenol; Oxyphenic acid; Pelagol grey C; O-Hydroquinone; O-Dioxybenzene; Pyrocatechine; Fouramine PCH; O-Benzenediol; Brenzcatechin; Pyrocatechin; pyrocatechol; Fourrine 68; Oxyphenate; Catechol; Catechol; Catechol
数据库引用编号
25 个数据库交叉引用编号
- ChEBI: CHEBI:33566
- ChEBI: CHEBI:18135
- KEGG: C15571
- PubChem: 289
- HMDB: HMDB0000957
- Wikipedia: Catechol
- MetaCyc: CATECHOL
- KNApSAcK: C00002644
- foodb: FDB001512
- chemspider: 13837760
- CAS: 120-80-9
- MoNA: RP012002
- MoNA: RP012003
- MoNA: RP012013
- MoNA: RP012001
- MoNA: RP012011
- MoNA: RP012012
- PubChem: 17396563
- PDB-CCD: CAQ
- NIKKAJI: J2.921A
- RefMet: Pyrocatechol
- BioNovoGene_Lab2019: BioNovoGene_Lab2019-427
- KEGG: C00090
- PubChem: 3390
- KNApSAcK: 18135
分类词条
相关代谢途径
Reactome(0)
BioCyc(18)
- diphenylamine degradation
- alkylnitronates degradation
- superpathway of aromatic compound degradation
- dibenzo-p-dioxin degradation
- phenol degradation I (aerobic)
- o-diquinones biosynthesis
- superpathway of aromatic compound degradation via 2-hydroxypentadienoate
- superpathway of aromatic compound degradation via 3-oxoadipate
- meta cleavage pathway of aromatic compounds
- 2-nitrophenol degradation
- catechol degradation II (meta-cleavage pathway)
- catechol degradation I (meta-cleavage pathway)
- aromatic compounds degradation via β-ketoadipate
- catechol degradation III (ortho-cleavage pathway)
- catechol degradation to β-ketoadipate
- mandelate degradation to acetyl-CoA
- benzene degradation
- indole-3-acetate degradation
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
41 个相关的物种来源信息
- 282720 - Achillea aspleniifolia: 10.1007/BF02908196
- 13329 - Achillea millefolium: 10.1007/BF02908196
- 282770 - Achillea virescens: 10.1007/BF02908196
- 681403 - Alchornea latifolia: 10.1016/S0367-326X(99)00133-1
- 117798 - Aloe ferox: 10.1271/BBB.60659
- 3702 - Arabidopsis thaliana: 10.1111/TPJ.14594
- 125587 - Bistorta officinalis: 10.4268/CJCMM20161721
- 313924 - Caesulia axillaris: 10.1007/BF01990427
- 13442 - Coffea: 10.1021/JF060460X
- 1219355 - Dactylorhiza hatagirea: 10.1248/CPB.47.1618
- 3039 - Euglena gracilis: 10.3389/FBIOE.2021.662655
- 3746 - Fragaria: 10.1016/J.JFF.2014.08.013
- 59324 - Gymnadenia conopsea: 10.1248/CPB.54.506
- 9606 - Homo sapiens: -
- 9606 - Homo sapiens: 10.1007/S11306-015-0840-5
- 65561 - Hypericum perforatum: 10.1055/S-2007-969352
- 124774 - Illicium fargesii: 10.1248/CPB.56.1201
- 1202800 - Illicium simonsii: 10.1248/CPB.56.1201
- 124778 - Illicium verum: 10.1248/CPB.56.1201
- 1219355 - Orchis latifolia: 10.1248/CPB.47.1618
- 254780 - Persicaria amphibia: 10.4268/CJCMM20161721
- 4837 - Phycomyces blakesleeanus: 10.1016/0031-9422(96)00146-X
- 77912 - Pinus densiflora: 10.3186/JJPHYTOPATH.50.166
- 77070 - Populus lasiocarpa: 10.1016/0031-9422(88)80758-1
- 113636 - Populus tremula:
- 3693 - Populus tremuloides: 10.1139/B94-060
- 55489 - Posidonia oceanica: 10.1016/S0031-9422(97)01118-7
- 22663 - Punica granatum: 10.3390/MOLECULES22101606
- 38942 - Quercus robur: 10.1055/S-2007-969352
- 50499 - Rorippa indica: 10.1016/0031-9422(95)00005-R
- 174651 - Rumex japonicus: 10.1248/BPB.28.2225
- 75712 - Salix interior: 10.1007/BF00566096
- 77065 - Salix purpurea: 10.1002/PCA.1220
- 409512 - Spiraea hypericifolia: 10.1007/BF00563836
- 1883 - Streptomyces: 10.1016/J.BIORTECH.2012.02.059
- 138033 - Vachellia nilotica: 10.1055/S-2007-969797
- 648865 - Vincetoxicum mongolicum: 10.1016/S0031-9422(00)95106-9
- 97415 - Viola arvensis: 10.1007/S11094-005-0104-1
- 29760 - Vitis vinifera: 10.1080/13102818.2006.10817302
- 552636 - Xanthium strumarium var. canadense: 10.1021/NP50041A038
- 569774 - 金线莲: -
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:
- PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。
文献列表
- Zuwu Tang, Xinxing Lin, Meiqiong Yu, Jinbei Yang, Shiqian Li, Ajoy Kanti Mondal, Hui Wu. A review of cellulose-based catechol-containing functional materials for advanced applications.
International journal of biological macromolecules.
2024 May; 266(Pt 2):131243. doi:
10.1016/j.ijbiomac.2024.131243
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Molecules (Basel, Switzerland).
2024 Mar; 29(6):. doi:
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The Science of the total environment.
2023 Nov; 898(?):166356. doi:
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Protein expression and purification.
2023 02; 202(?):106195. doi:
10.1016/j.pep.2022.106195
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Biochemical pharmacology.
2023 02; 208(?):115385. doi:
10.1016/j.bcp.2022.115385
. [PMID: 36535528] - Roelant Hilgers, Judith Bijlsma, Luana Malacaria, Jean-Paul Vincken, Emilia Furia, Wouter J C de Bruijn. Transition metal cations catalyze 16O/18O exchange of catechol motifs with H218O.
Organic & biomolecular chemistry.
2022 11; 20(46):9093-9097. doi:
10.1039/d2ob01884e
. [PMID: 36378241] - Ana Amić, Denisa Mastiľák Cagardová. DFT Study of the Direct Radical Scavenging Potency of Two Natural Catecholic Compounds.
International journal of molecular sciences.
2022 Nov; 23(22):. doi:
10.3390/ijms232214497
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Environmental science and pollution research international.
2022 May; ?(?):. doi:
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Molecules (Basel, Switzerland).
2022 May; 27(10):. doi:
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2022; 40(19):9067-9080. doi:
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Scientific reports.
2021 10; 11(1):21049. doi:
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Cellular and molecular biology (Noisy-le-Grand, France).
2021 Sep; 67(2):50-55. doi:
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Journal of materials chemistry. B.
2021 09; 9(34):6825-6835. doi:
10.1039/d1tb01164b
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ACS applied materials & interfaces.
2021 Aug; 13(33):39126-39134. doi:
10.1021/acsami.1c12176
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Biochemistry.
2021 08; 60(32):2492-2507. doi:
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Advanced materials (Deerfield Beach, Fla.).
2021 May; 33(18):e2007758. doi:
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Journal of oleo science.
2021 May; 70(5):607-613. doi:
10.5650/jos.ess20294
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Cell reports.
2021 04; 35(4):109040. doi:
10.1016/j.celrep.2021.109040
. [PMID: 33910017] - Fei Zhou, Robert L Last, Eran Pichersky. Degradation of salicylic acid to catechol in Solanaceae by SA 1-hydroxylase.
Plant physiology.
2021 04; 185(3):876-891. doi:
10.1093/plphys/kiaa096
. [PMID: 33793924] - Peng Xiao, Wei Yan, Lu Gou, Ya-Ni Zhong, Liangliang Kong, Chao Wu, Xin Wen, Yuan Yuan, Sheng Cao, Changxiu Qu, Xin Yang, Chuan-Cheng Yang, Anjie Xia, Zhenquan Hu, Qianqian Zhang, Yong-Hao He, Dao-Lai Zhang, Chao Zhang, Gui-Hua Hou, Huanxiang Liu, Lizhe Zhu, Ping Fu, Shengyong Yang, Daniel M Rosenbaum, Jin-Peng Sun, Yang Du, Lei Zhang, Xiao Yu, Zhenhua Shao. Ligand recognition and allosteric regulation of DRD1-Gs signaling complexes.
Cell.
2021 02; 184(4):943-956.e18. doi:
10.1016/j.cell.2021.01.028
. [PMID: 33571432] - In Kyung Yoo, Keumyeon Kim, Gawon Song, Mi-Young Koh, Moon Sue Lee, Abdullah Özgür Yeniova, Haeshin Lee, Joo Young Cho. Endoscopic application of mussel-inspired phenolic chitosan as a hemostatic agent for gastrointestinal bleeding: A preclinical study in a heparinized pig model.
PloS one.
2021; 16(5):e0251145. doi:
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. [PMID: 33989307] - Qincao Chen, Jiang Shi, Bing Mu, Zhen Chen, Weidong Dai, Zhi Lin. Metabolomics combined with proteomics provides a novel interpretation of the changes in nonvolatile compounds during white tea processing.
Food chemistry.
2020 Dec; 332(?):127412. doi:
10.1016/j.foodchem.2020.127412
. [PMID: 32623128] - Veronica F Salau, Ochuko L Erukainure, Neil A Koorbanally, Md Shahidul Islam. Catechol protects against iron-mediated oxidative brain injury by restoring antioxidative metabolic pathways; and modulation of purinergic and cholinergic enzymes activities.
The Journal of pharmacy and pharmacology.
2020 Dec; 72(12):1787-1797. doi:
10.1111/jphp.13352
. [PMID: 32902887] - Ludovica Antiga, Sonia Roberta La Starza, Cecilia Miccoli, Simone D'Angeli, Valeria Scala, Marco Zaccaria, Xiaomei Shu, Gregory Obrian, Marzia Beccaccioli, Gary A Payne, Massimo Reverberi. Aspergillus flavus Exploits Maize Kernels Using an 'Orphan' Secondary Metabolite Cluster.
International journal of molecular sciences.
2020 Nov; 21(21):. doi:
10.3390/ijms21218213
. [PMID: 33153018] - Duraiyarasu Maheshwaran, Thavasilingam Nagendraraj, T Sekar Balaji, Ganesan Kumaresan, S Senthil Kumaran, Ramasamy Mayilmurugan. Smart dual T1 MRI-optical imaging agent based on a rhodamine appended Fe(III)-catecholate complex.
Dalton transactions (Cambridge, England : 2003).
2020 Oct; 49(41):14680-14689. doi:
10.1039/d0dt02364g
. [PMID: 33064113] - Yu Jin Kim, Eunjin Sohn, Joo-Hwan Kim, MinKyun Na, Soo-Jin Jeong. Catechol-Type Flavonoids from the Branches of Elaeagnus glabra f. oxyphylla Exert Antioxidant Activity and an Inhibitory Effect on Amyloid-β Aggregation.
Molecules (Basel, Switzerland).
2020 Oct; 25(21):. doi:
10.3390/molecules25214917
. [PMID: 33114256] - Yinghui Ma, Lijun Li, Mukesh Kumar Awasthi, Haixia Tian, Meihuan Lu, Mallavarapu Megharaj, Yalei Pan, Wenxiang He. Time-course transcriptome analysis reveals the mechanisms of Burkholderia sp. adaptation to high phenol concentrations.
Applied microbiology and biotechnology.
2020 Jul; 104(13):5873-5887. doi:
10.1007/s00253-020-10672-2
. [PMID: 32415321] - Yuting Li, Haiping Qi, Meiqi Fan, Zixing Zhu, Shijie Zhan, Lin Li, Bing Li, Xia Zhang, Xianglong Zhao, Jingjing Ma, Lifeng Wang. Quantifying the efficiency of o-benzoquinones reaction with amino acids and related nucleophiles by cyclic voltammetry.
Food chemistry.
2020 Jul; 317(?):126454. doi:
10.1016/j.foodchem.2020.126454
. [PMID: 32113140] - Kristen Van Gelder, Taylor Forrester, Tariq A Akhtar. Evidence from stable-isotope labeling that catechol is an intermediate in salicylic acid catabolism in the flowers of Silene latifolia (white campion).
Planta.
2020 Jun; 252(1):3. doi:
10.1007/s00425-020-03410-5
. [PMID: 32514846] - Jiayi Sun, Toshihiro Murata, Hideyuki Shigemori. Inhibitory activities of phenylpropanoids from Lycopus lucidus on amyloid aggregation related to Alzheimer's disease and type 2 diabetes.
Journal of natural medicines.
2020 Jun; 74(3):579-583. doi:
10.1007/s11418-020-01398-6
. [PMID: 32219646] - Weidong Dai, Zhengyan Hu, Dongchao Xie, Junfeng Tan, Zhi Lin. A novel spatial-resolution targeted metabolomics method in a single leaf of the tea plant (Camellia sinensis).
Food chemistry.
2020 May; 311(?):126007. doi:
10.1016/j.foodchem.2019.126007
. [PMID: 31855776] - Petteri Parkkila, Tapani Viitala. Partitioning of Catechol Derivatives in Lipid Membranes: Implications for Substrate Specificity to Catechol-O-methyltransferase.
ACS chemical neuroscience.
2020 03; 11(6):969-978. doi:
10.1021/acschemneuro.0c00049
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Archives of microbiology.
2020 Mar; 202(2):421-426. doi:
10.1007/s00203-019-01743-8
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Ecotoxicology and environmental safety.
2020 Feb; 189(?):109953. doi:
10.1016/j.ecoenv.2019.109953
. [PMID: 31759741] - Romina Romero, David Contreras, Mónica Sepúlveda, Nataly Moreno, Cristina Segura, Victoria Melin. Assessment of a Fenton reaction driven by insoluble tannins from pine bark in treating an emergent contaminant.
Journal of hazardous materials.
2020 01; 382(?):120982. doi:
10.1016/j.jhazmat.2019.120982
. [PMID: 31450209] - Dorian Blondeau, Annabelle St-Pierre, Nathalie Bourdeau, Julien Bley, André Lajeunesse, Isabel Desgagné-Penix. Antimicrobial activity and chemical composition of white birch (Betula papyrifera Marshall) bark extracts.
MicrobiologyOpen.
2020 01; 9(1):e00944. doi:
10.1002/mbo3.944
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Molecules (Basel, Switzerland).
2019 Dec; 24(23):. doi:
10.3390/molecules24234407
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Pigment cell & melanoma research.
2019 11; 32(6):766-776. doi:
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Colloids and surfaces. B, Biointerfaces.
2019 Nov; 183(?):110413. doi:
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. [PMID: 31401461] - Maofang He, Yinmao Wei, Rong Wang, Chunyang Wang, Bo Zhang, Lu Han. Boronate affinity magnetic nanoparticles with hyperbranched polymer brushes for the adsorption of cis-diol biomolecules.
Mikrochimica acta.
2019 09; 186(10):683. doi:
10.1007/s00604-019-3785-y
. [PMID: 31529296] - Qian-Yun Han, Fang Liu, Mo Li, Kun-Li Wang, Yuan-Ying Ni. Comparison of biochemical properties of membrane-bound and soluble polyphenol oxidase from Granny Smith apple (Malus × domestica Borkh.).
Food chemistry.
2019 Aug; 289(?):657-663. doi:
10.1016/j.foodchem.2019.02.064
. [PMID: 30955661] - Chengyuan Su, Yuxiang Lu, Qiujin Deng, Shenglong Chen, Gange Pang, Wuyang Chen, Menglin Chen, Zhi Huang. Performance of a novel ABR-bioelectricity-Fenton coupling reactor for treating traditional Chinese medicine wastewater containing catechol.
Ecotoxicology and environmental safety.
2019 Aug; 177(?):39-46. doi:
10.1016/j.ecoenv.2019.03.112
. [PMID: 30959311] - Ivan V Smolyaninov, Olga V Pitikova, Eugenia O Korchagina, Andrey I Poddel'sky, Georgy K Fukin, Svetlana A Luzhnova, Andrey M Tichkomirov, Elena N Ponomareva, Nadezhda T Berberova. Catechol thioethers with physiologically active fragments: Electrochemistry, antioxidant and cryoprotective activities.
Bioorganic chemistry.
2019 08; 89(?):103003. doi:
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Journal of biotechnology.
2019 Jul; 300(?):48-54. doi:
10.1016/j.jbiotec.2019.05.008
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Colloids and surfaces. B, Biointerfaces.
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Molecular nutrition & food research.
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Cellular and molecular biology (Noisy-le-Grand, France).
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Acta biomaterialia.
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Plant physiology.
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European journal of medicinal chemistry.
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Biosensors & bioelectronics.
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Analytical chemistry.
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ACS applied materials & interfaces.
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Talanta.
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